Sodium Bicarbonate → HCID 57809756, compound

HRID 2105993Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH3:20])=[C:6]([C:8]([CH3:18])([CH3:17])[CH2:9][C:10]2([C:13]([F:16])([F:15])[F:14])[CH2:12][O:11]2)[CH:7]=1.[OH:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]=[CH:24][C:23]=1[CH2:32][OH:33].[O-]CC.[Na+].C(=O)(O)[O-].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH3:20])=[C:6]([C:8]([CH3:18])([CH3:17])[CH2:9][C:10]([OH:11])([C:13]([F:16])([F:15])[F:14])[CH2:12][N:25]2[C:26]3[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:22](=[O:21])[C:23]([CH2:32][OH:33])=[CH:24]2)[CH:7]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a suspension of 2-[2-(5-fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane (344 mg) and 4-hydroxy-3-hydroxymethylquinoline (412 mg) in anhydrous ethanol (2.5 mL) was added sodium ethoxide (21 wt. % solution in ethanol, 439 μL). After heating at 85° C. for 17 hours, the reaction mixture was poured into saturated aqueous sodium bicarbonate and extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography with silica gel (eluted with 80%-100% ethyl acetate-hexanes) to give the title compound as a white solid (405 mg), m.p. 183° C.-184° C.

Workup

extractionextracted twice with ethyl acetate
dry with materialThe combined organic phases were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography with silica gel (eluted with 80%-100% ethyl acetate-hexanes)

Sources & evidence

ORD record: ord-cc71d8c7790e4f53aee0c54a84bb6fbf
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579469B2

Reaction notes

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